3-amino-6-chloropyrazine-2-carboxylicacid

DIPEA (200 muIota, 1.15 mmol) was added to a solution of 3-amino-6-chloropyrazine-2- carboxylic acid (50 mg, 0.29 mmol), 2-(aminomethyl)-1-ethyl-6-methoxy-3-methyl-1H-1 , 3- benzodiazol-3-ium iodide, Intermediate 13 (100 mg, 0.29 mmol) and HBTU (142 mg, 0.37 mmol) in anhydrous DMF (1 ml). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated under a flow of nitrogen to afford the crude product as an oil. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCN:H20 + 0.1 % formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and lyophilised to yield the product as an off-white solid (84 mg, 58%).1H NMR (250 MHz, DMSO-de) delta 9.57 (t, J = 5.3 Hz, 1 H), 8.38 (s, 1 H), 7.93 (d, J = 9.1 Hz, 1 H), 7.66 (s, 2H), 7.57 (d, J = 2.2 Hz, 1 H), 7.29 (dd, J = 9.1 , 2.3 Hz, 1 H), 4.99 (d, J = 5.3 Hz, 2H), 4.62 (q, J = 7.0 Hz, 2H), 4.09 (s, 3H), 3.91 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H). LC/MS (System C): m/z (ESI+) = 375 [M(35CI)+], 377 [M(37CI)+]), R = 1.83 min, UV purity = 100%.A mixture of 3-amino-6-chloro-pyrazine-2-carbox-ylic acid (26.0 mg; 0.150 mmol), the amine intermediateIX.3 (100 mg; 0.151 mmol), TETU (53.0 mg; 0.165 mmol), triethylamine (63.2 jtl; 0.450 mmol) and DMF (5.0 ml) isstirred at tt. overnight. Volatiles are evaporated and theresidue is purified by RP-HPLC (Cl 8; water-ACN-TFA).10130] C25H33C1N7O5SxC2O2F3 ESI Mass spectrum:mlz=590 [M+H]+10131] HPLC analytics: RT=0.42 mm (HPLC method D)A mixture of

Molecular Weight:173.56
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:172.9992041
Monoisotopic Mass:172.9992041
Topological Polar Surface Area:89.1
Heavy Atom Count:11
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes